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So the "Castling" puzzle has to do with looking for notes and documents that somehow have a cipher that's formatted the same way. For example letters arranged vertically with blanks or gaps. For example one of the notes found in the locker room.
But to do a "Castle" move in the game, you don't do it like you would in an actual Chess game, you Castle by just picking the Chess Power-Ups via completing the Chessboard puzzle like normal. (Rook then King or King then Rook.) So you need to complete the normal chess puzzle at least twice. It's basically moon Logic so I don't really mind spoiling that for you. The puzzle leads to more puzzles btw and if you need help with the Ciphers you can always google.
The second spoiler, yeah I don't think I'd ever make that leap. I wonder if there is ANYTHING that points to that logic anyone has found?
Some of the puzzles are just moon logic sadly. I only resort to google if I get stumped and have no idea how to continue. A lot of the puzzles are well designed though and just require a little detective work. The classrooms for example have a lot of knowledge you should be paying attention to for multiple puzzles.
Far as the Castling puzzle goes, unless there's a letter delivered to the mailroom explaining the situation that I haven't encountered, it's just moon logic. (The letters delivered to the mailroom though basically feel like googling as they fully explain puzzles which isn't super fun)
I only have 12 letters in the mailroom and judging by the remaining space there may be ~4 more so I'll try to check them as well.